Claims
- 1. A caged binding member compound having the formula: ##STR30## wherein X and Z are selected from the group consisting of (a) hydrogen,
- (b) oxycarbonyls of lower alkyl, aryl, and benzyl groups,
- (c) a nitroveratryloxycarbonyl group,
- (d) a nitropiperonyloxycarbonyl group where Z is hydrogen and R is p-nitrophenyl formate,
- (e) ##STR31## wherein R.sub.1 and R.sub.2 are hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, sulfonate, formamido or phosphido groups,
- (f) ##STR32## wherein R.sub.1 and R.sub.2 are hydrogen, lower alkyl, aryl, benzyl, pyrenyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido or phosphido groups, and R.sub.3 and R.sub.4 are hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido or phosphido groups,
- (g) ##STR33## wherein R.sub.1 and R.sub.2 are hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido or phosphido groups, and
- (h) ##STR34## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido or phosphido groups, provided that when X is hydrogen, Z is not hydrogen or methyloxycarbonyl and provided that when Z is hydrogen, X is not hydrogen or methyloxycarbonyl;
- R is selected from the group consisting of hydrogen, lower alkyl, aryl, carboxylate lower alkyl formate, aryl formate, methyl formate, p-nitrophenyl formate, formamide, N-alkylformamide, N-succinimidyl, hydroxyl, alkoxyl, thiol, thioether, disulfide, hydrazide and amine groups, provided that when X or Z is methyloxycarbonyl, R is not methyl formate;
- U is O, S or NH;
- Y is selected from the group consisting of sulfur, oxygen, methylene, carbonyl, sulfinyl and sulfonyl groups, or Y represents two hydrogens attached to the respective carbons;
- n=0-7;
- or acid addition salts of the compound.
- 2. A compound as in claim 1 wherein U is O, Y is sulfur, and n=4.
- 3. A compound as in claim 1 wherein one of X and Z is a nitroveratryloxycarbonyl group.
- 4. A compound as in claim 1 wherein one of X and Z has the formula: ##STR35## wherein R.sub.1 and R.sub.2 are hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, sulfonate, formamido or phosphido groups.
- 5. A compound as in claim 1 wherein X is 6-nitroveratryloxycarbonyl; Z is hydrogen; and R is methyl formate.
- 6. A compound as in claim 1 wherein X is 6-nitroveratryloxycarbonyl; Z is hydrogen; and R is p-nitrophenyl formate.
- 7. A compound as in claim 1 wherein X is 6-nitropiperonyloxycarbonyl, Z is hydrogen; and R is p-nitrophenyl formate.
- 8. A compound as in claim 1 wherein one of X and Z is ##STR36## wherein R.sub.1 and R.sub.2 are hydrogen, lower alkyl, aryl, benzyl, pyrenyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido or phosphido groups, and R.sub.3 and R.sub.4 are hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido or phosphido groups.
- 9. A caged binding member compound having the formula selected from the group consisting of: ##STR37## wherein X is selected from the group consisting of (a) hydrogen,
- (b) lower alkyl,
- (c) aryl,
- (d) benzyl,
- (e) substituted benzyl selected from the group consisting of ##STR38## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are selected from the group consisting of hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido and phosphido groups provided that R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are not all hydrogen, and ##STR39## wherein R.sub.1 and R.sub.2 are selected from the group consisting of hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido and phosphido groups.
- (f) nitroveratryl,
- (g) 6-nitroveratryl,
- (h) 6-nitroveratryloxycarbonyl, and
- (i) 6-nitropiperonyloxycarbonyl where U or W is hydrogen;
- U and W are selected from the group consisting of hydrogen, lower alkyl, aryl, benzyl and substituted benzyl selected from the group consisting of ##STR40## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are selected from the group consisting of hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido and phosphido groups provided that R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are not all hydrogen, and ##STR41## wherein R.sub.1 and R.sub.2 are selected from the group consisting of hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido and phosphido groups, provided that only one of U or W is present;
- R is selected from the group consisting of hydrogen, lower alkyl, aryl, carboxylate, alkyl formate, aryl formate, formamide, N-alkyl formamide, N-succinimidyl, hydroxyl, alkoxyl, thiol, thioether, disulfide, hydrazide and amine groups;
- Y is selected from the group consisting of sulfur, oxygen, methylene, carbonyl, sulfinyl and sulfonyl groups, or Y represents two hydrogens attached to the respective carbons; and n=0-7; or acid addition salts of the compound.
- 10. A compound as in claim 9 wherein Y is sulfur and n=4.
- 11. A compound as in claim 9 wherein one of X, U or W has the formula: ##STR42## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are selected from the group consisting of hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido and phosphido groups provided that R.sub.1, R.sub.2, R.sub.4 are not all hydrogen.
- 12. A compound as in claim 11 wherein R.sub.1 and R.sub.2 are methoxy.
- 13. A compound as in claim 11 wherein R.sub.3 and R.sub.4 are methyl.
- 14. A compound as in claim 9 wherein X is a nitroveratryl group.
- 15. A compound as in claim 9, wherein X has the formula: ##STR43## wherein R.sub.1 and R.sub.2 are selected from the group consisting of hydrogen, lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thiol, thioether, amino, nitro, carboxyl, formate, formamido and phosphido groups.
- 16. A compound as in claim 9 wherein X is 6-nitroveratryl; U or W is hydrogen: and R is methyl formate.
- 17. A compound as in claim 9 wherein X is 6-nitroveratryloxycarbonyl hydrogen; and R is p-nitrophenyl formate.
- 18. A compound as in claim 9 wherein X is 6-nitropiperonyloxycarbonyl and U or W is hydrogen.
- 19. A compound as in claim 9 wherein X is a substituted benzyl group, and R is methyl formate or p-nitrophenyl formate.
- 20. A compound as in claim 8 wherein R.sub.1 and R.sub.2 are methoxy.
- 21. A compound as in claim 8 wherein R.sub.3 and R.sub.4 are methyl.
Parent Case Info
This is a division of application Ser. No. 07/612,671, filed Nov. 13, 1990, now U.S. Pat. No. 5,252,473 which is a continuation-in-part of application Ser. No. 07/435,316, filed Nov. 13, 1989, now abandoned.
US Referenced Citations (24)
Foreign Referenced Citations (1)
Number |
Date |
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019788 |
May 1980 |
EPX |
Divisions (1)
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Number |
Date |
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Parent |
612671 |
Nov 1990 |
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Continuation in Parts (1)
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Number |
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435316 |
Nov 1989 |
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